Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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Vacation Dresses & Outfits for Effortless Getaways
Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.
Easy, Packable Styles
Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.
Day-to-Night Versatility
Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.
Resort & Beach Essentials
Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.
Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.
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Pick Me Floral Lace-Up Maxi Dress
This floral maxi dress will be the first pick in your closet! It features a sleeveless V-neckline with a knotted bust, spaghetti straps that creates the open lace-up back design, and a flowy slim silhouette. Complete the look in cute new sandals for a baby shower or casual lunch out!
Fit & Features
- Sleeveless V-neckline, knotted bust
- Spaghetti straps
- Lace-up open back
- Flowy slim silhouette
- Maxi-length hem
- Floral print, breezy woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4947
Category Name: Vacation Looks
Price: $5.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fresh In Paisley Floral A-Line Dress
Serve your closet a fresh style by adding this paisley floral short dress to it! Featuring a sleeveless V-neckline, sleek bungee spaghetti straps, a flattering A-line silhouette, and a flirty slit hem. Complete the look in trendy sandals for an afternoon in the city!
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- A-line silhouette
- Short-length hem, slit accent
- Paisley floral print
- Smooth stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4943
Category Name: Vacation Looks
Price: $5.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beach Boardwalk Stroll Cutout Denim Romper
This adorable cutout denim romper is perfect for a stroll along a beach boardwalk this summer! It features a sleeveless plunging neckline with ruching, cross-front halter spaghetti straps with a tie-back design, a bold front waist cutout, a high-rise waist, and fitted shorts. The cotton-blend denim fabric offers a moderate stretch. Style with slip-on sandals and trendy shades.
Fit & Features
- Sleeveless plunging neckline, ruching
- Cross-front halter spaghetti straps, tie-back design
- Front waist cutout, high-rise waist
- Fitted shorts
- Back zipper, hook and eye closure
- Cotton-blend denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0343
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Cruise Tropical Print Strapless Jumpsuit
Create a picture-perfect 'fit for a sunset cruise with this tropical-printed jumpsuit! Featuring a strapless straight-across neckline, a ruched high waist, a flattering wide-leg silhouette, and an all-over palm leaf print, this jumpsuit will capture those summer vibes. Style with espadrille sandals.
Fit & Features
- Strapless straight-across neckline
- Ruched high waist
- Wide-leg silhouette
- Tropical palm leaf print
- Stretchy knit fabric, bust lining
- Runs true to size
Style Number/Barcode: 06502-2350
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Summer Style Ditsy Floral Bustier Top
Step out this summer in flirty casual 'fits with this ditsy floral bustier top. It features a sleeveless square neckline, tie-shoulder spaghetti straps, structured underwire, front hook and eye closures, and a cropped, ruffled hem. The ditsy floral printed knit fabric offers a moderate stretch. Style with light-wash denim and slide-on sandals.
Fit & Features
- Sleeveless square neckline
- Tie-shoulder spaghetti straps
- Structured underwire, front hook and eye closures
- Cropped ruffled hem, fitted silhouette
- Ditsy floral print
- Ribbed knit fabric, front lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4657
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Stylish Ribbed Knit Midi Dress
This simple yet chic ribbed knit midi dress is the casually stylish staple you need. It features a sleeveless scoop neckline, thin tank shoulder straps, a midi-length hem, and a curve-hugging silhouette. The lined knit fabric offers plenty of stretch. Complete the look with a denim jacket and clear mules.
Fit & Features
- Sleeveless scoop neckline
- Thin tank shoulder straps
- Midi-length hem
- Form-hugging fit
- Lined ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5077
Category Name: Vacation Looks
Price: $5.97 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Whirlwind Romance Floral Abstract Maxi Dress
This maxi dress is giving goddess in the wild. The sheer mesh and abstract floral print bring soft drama to any scene, whether it's brunch or rooftop party soirees!
Fit & Features
- Abstract floral print, mesh lined fabric
- Sweetheart neckline, padded bra cups, ruched bust seam
- Spaghetti straps
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-000242
Category Name: Vacation Looks
Price: $7.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect And Posh Pearl Choker Necklace
Perfect and posh will be your vibe with this pretty pearl choker necklace! It features a thin metal zig-zag design with round faux pearl embellishments and small metal bead accents. Style with duster earrings for a complete glam look.
Fit & Features
- Thin metal zig-zag design
- Round faux pearls
- Small metal bead accents
- Adjustable chain, lobster clasp closure
Style Number/Barcode: 07002-1490
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Marvelous Style Marble Print Maxi Dress
Showcase a marvelous style in this trendy marble print maxi dress! It features a sleeveless square neckline, spaghetti straps, an asymmetric side cutout at the waist to add a sultry vibe, ruching down one side seam with an adjustable drawstring, an asymmetric maxi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The all-over eye-catching marble print pattern on the smooth and stretchy knit fabric will draw all the attention to you! Complete your summer party look with clear heels.
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Asymmetric side cutout at the waist
- Ruching down one side seam, adjustable drawstring
- Asymmetric maxi-length hem, high side slit, curve-hugging fit
- Marble print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5119
Category Name: Vacation Looks
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Boho Dream Cropped Tie-Front Top
Create a dreamy boho-chic look with this cropped tie-front top! It features short sleeves, a V-neckline with a tie-front design, and a fitted cropped hem. The airy gauze fabric has no stretch. Style with a trendy bralette and high-rise denim shorts for casual weekend plans.
Fit & Features
- Short sleeves
- V-neckline
- Tie-front design
- Fitted cropped hem
- Lightweight gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1180
Category Name: Vacation Looks
Price: $11.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Staple Mock Neck Tank Top
This basic ribbed knit tank top is a casual staple to create the cutest looks! It features a sleeveless mock neckline, tank shoulder straps, and a fitted cropped hem. The lightweight ribbed knit fabric offers plenty of stretch. Style with your favorite pair of denim and hoop earrings.
Fit & Features
- Sleeveless mock neckline
- Tank shoulder straps
- Fitted cropped hem
- Ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1587
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend By The Bay Cotton Wide-Leg Pants
Create a chic relaxed look for a weekend by the bay in these lightweight cotton wide-leg pants. They feature an elasticized high-rise waist with an adjustable front drawstring, dual front pockets, and a casual wide-leg silhouette. The cotton fabric has no stretch. Pair with a crop top and sandals.
Fit & Features
- Elasticized high-rise waist
- Adjustable front drawstring
- Dual front pockets
- Wide-leg silhouette
- Cotton fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0773
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Sultry Vibes Cutout Maxi Dress
Bring the casual sultry vibes to your weekend plans with this curve-hugging maxi dress. It features a sleeveless sweetheart neckline with a twist-front design, spaghetti straps, a bold waist cutout at the front, a maxi-length hem with a chic back slit accent, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules for drinks with the girls.
Fit & Features
- Sleeveless sweetheart neckline, twist-front design
- Spaghetti straps
- Waist cutout
- Maxi-length hem, back slit
- Bodycon fit
- Ribbed knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5186
Category Name: Vacation Looks
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Chic Cutout Midi Sweater Dress
Create the perfect casual chic look with this of-the-moment sweater dress. It features a sleeveless scoop neckline with contrast piping, thin tank shoulder straps, a front waist cutout with matching contrast piping, a midi-length hem with a front slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules.
Fit & Features
- Sleeveless scoop neckline, contrast piping
- Thin tank shoulder straps
- Front waist cutout, contrast piping
- Midi-length hem, front slit
- Curve-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1700
Category Name: Vacation Looks
Price: $44.90
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Happy Face Statement Sunglasses
Complete your fab summer festival 'fits with these trendy statement sunnies! The sunglasses feature round-tinted lenses with a heart-eyed happy face cutout design, sleek metal arms, and rubber nose pads for support. Style with a rhinestone choker necklace.
Fit & Features
- Round-tinted lenses
- Heart-eyed happy face cutout design
- Thin metal arms
- Rubber nose pads
- Polycarbonate, blocks 100% UV
Style Number/Barcode: 07008-1032
Category Name: Vacation Looks
Price: $2.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Total Heartbreaker Statement Sunglasses
You'll be a total heartbreaker this season in these fabulous statement sunglasses. They feature heart-shaped black-tinted lenses with a dripping design, sleek metal arms, and rubber nose pads for support. Style with a layered choker necklace and hoop earrings for a summer concert.
Fit & Features
- Heart-shaped black-tinted lenses
- Dripping design
- Thin metal arms
- Rubber nose pads
- 100% UV protection
Style Number/Barcode: 07008-1034
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Butterfly Babe Rhinestone Statement Sunglasses
Style up your summer festival 'fits with these trendy statement sunglasses! They feature a butterfly design with no frame, pink flower accents, gemstones, and rhinestones on each side, sleek metal arms, and rubber nose pads for support. Pair with charm earrings and a choker necklace!
Fit & Features
- Butterfly design, no frame
- Pink tinted lenses
- Pink flower accents, gemstones, rhinestones
- Thin metal arms
- Rubber nose pads
- 100% UV protection
Style Number/Barcode: 07008-1035
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Edgy Flair Flat Top Square Sunglasses
Give your summer 'fits an edgy flair with these cool shades. The sunglasses feature a flat top square-shaped design, a plastic frame with metal geometric accents on each side, and tinted lenses. Style with a cropped denim jacket.
Fit & Features
- Flat top
- Square-shaped design
- Plastic frame
- Metal geometric side accents
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1020
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Girl High Rise Wide Leg Pants
Showcase island vibes on vacation in these must-have tropical pants perfect for chilling under the cabana with a cocktail in hand! They feature a flattering high-rise waist, slim hip-hugging fit, a wide-leg silhouette, and a breezy palm print. Complete the look in platform sandals.
Fit & Features
- High-rise waist
- Slim hip-hugging fit
- Wide-leg silhouette
- Palm print
- Knit fabric
- Runs true to size
Style Number/Barcode: 06502-2355
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fun In The Sun Raffia Platform Block Heels
Have fun in the sun in these cute raffia heels designed to elevate your look with a platform sole, block heel, and a cushioned insole that keeps you comfortable all day!
Fit & Features
- 4.5" Block heel
- Almond toe, crisscross toe straps
- Adjustable ankle strap, buckle closure
- Platform sole
- Luxe fit cushioned insole
- Raffia material
- Runs true to size
Style Number/Barcode: 07401-5331
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ultra-Chic Small Rectangular Frame Sunglasses
Show off an ultra-chic look in these sleek of-the-moment sunglasses. They feature a small geometric rectangular-shaped design with a plastic frame, metal square-shaped accents on the arms, and tinted lenses. Style with a crossbody bag.
Fit & Features
- Small geometric rectangular-shaped design
- Plastic frame
- Metal square-shaped accents on the arms
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1030
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Level Up Rectangular Frame Sunglasses
Level up your look for the summer season with these trendy shades! The sunglasses feature a geometric rectangular-shaped design with a plastic frame and tinted lenses. Style with a layered charm necklace.
Fit & Features
- Geometric rectangular-shaped design
- Plastic frame
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1029
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Heat Things Up Cutout Mini Dress
Heat things up in this showstopping bodycon mini dress on vacation or at a summer party! It features a sweetheart neckline, spaghetti straps that crisscross in the back, dual front center O-ring inserts and cutout accents, side ruched seams, and a fitted hem. Complete the look with geo-shaped earrings and a layered necklace.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps, crisscross back
- Dual front center O-ring inserts, cutout accents
- Bodycon silhouette, side ruched seams
- Mini-length fitted hem
- Double-lined brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-5137
Category Name: Vacation Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend State Of Mind Long Cotton Vest
Get into a weekend state of mind with this chic long cotton vest. It features a sleeveless bodice with a lapel collar, a button-down front, a thin tie-front detail, front pockets, and a long-line hem with a fitted silhouette. Layer this lightweight vest over a mini dress with espadrille sandals.
Fit & Features
- Sleeveless bodice, lapel collar
- Button-down front
- Thin tie-front detail
- Dual front pockets
- Long-line hem, fitted silhouette
- Cotton fabric, sewn-in woven lining
- Runs true to size
Style Number/Barcode: 06204-1595
Category Name: Vacation Looks
Price: $6.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance